
Family-friendly holiday rentals in Hampshire County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Hampshire County
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

The Creation Station
Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

The cozy clubhouse
Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

Refined cozy studio retreat – Under the Hemlocks
Escape to a tranquil boutique‑style studio guest suite under the hemlocks — a refined bijou space, small in scale yet elegantly detailed and entirely your own. Sink into the dreamy bed, soak in the deep clawfoot tub, venture to the unique off‑grid Writer’s Retreat, or steal a quiet moment in the private courtyard. Elegant furnishings, fine linens, a bespoke kitchenette, and curated amenities create a serene haven — minutes to Amherst Center, Amherst College, UMass, and the Emily Dickinson Museum

Luxurious and Sunny Bedroom Suite!
Luxurious and sunny suite with private bath, separate entrance, Tv/sitting room, reading nook, desk/work area, and coffee bar. 6 blocks to town, and beautiful views of Skinner Mt. Decorated with handcrafted wood furniture by one of Northampton's most recognized furniture makers. Private patio, large backyard with pick-your-own raspberries and blueberries. The suite has a private parking space, and is conveniently located near the bike path, and route 91. Come relax, and explore Northampton.

Serene 1-br suite on 75 acre horse property
Find your peaceful retreat in our 1-bedroom suite, situated on a serene 75-acre horse property with scenic nature trails. Enjoy a private entrance, dedicated workspace, and complimentary high-speed WiFi, making it an ideal haven for remote workers. Take in the picturesque views of our horse pastures, with up to 20 horses, right from your windows. Our property is nestled in the woods, about 1/3 mile from the main road. Located near Amherst, Hampshire, UMass, Smith, and Mt. Holyoke colleges.

Separate apt, 1 mile from downtown, 1 guest only
This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. We’re located in Village Hill.

The Floating Library: private hiker's hideaway
Spacious enough for a small family, cozy enough for a couple, a perfect alternative to a hotel, for exploring New England, or holing up to finish that book (reading or writing). TFL is a welcoming, above the garage in-law suite with a private entrance, full kitchen, full bath, laundry room, and lots of magical touches that will make your stay comfortable, unique and memorable. The location is right at the foot the hiking trails of Mt. Tom, a 20 min walk to idyllic downtown Easthampton.

Sweet Retreat minutes from Northampton & Amherst
Our home is in Hadley, MA which is less than 5 minutes from Amherst and 10 minutes from Northampton. Amherst is home to the flagship campus of University of Massachusetts, Amherst College and Hampshire College. Northampton is home to Smith College and in nearby South Hadley is the campus of Mount Holyoke College. Hadley is known for it's farmlands and open spaces. Northampton is a vibrant arts community that overflows with great restaurants, shops, cafes, music venues and galleries.

Light filled three bedroom apartment DT Florence!
Open floor plan duplex with beautiful back yard that has a patio, dog run, chickens, grill, fire pit, and fruit trees! One block from the corner store and the Pie Bar. If you enjoy cycling the bike path abuts the back of the property! Quiet neighborhood, pet and kid friendly one block from downtown Florence. Look Park is a mile down the bike path. Plenty to do if the weather is not cooperating. Fully appointed kitchen to make cookies, home made ice cream, plenty of games and records.

*Spacious Sweet 2 Bedroom Apt, 5 College area*
RED DOOR GETAWAY- 1000 Sq. ft. single floor spacious & bright apartment, fully stocked eat-in kitchen with coffee set up, stove, dishwasher & refrigerator. Master bdrm with queen bed, en suite. 2nd bdrm with 2 twin beds. All doors are 36" wide. 3/4 bathroom has handicap accessible shower. High speed internet , smart TV with Roku. Washer & dryer shared with owners. Private entrance, plenty of off street parking. Private back deck. Owners on site, available at all times.

Vintage 3BR Farmhouse | Near Town + Mount Holyoke
Enjoy the charm of an 1875 farmhouse with modern comforts in this spacious 3-bedroom, 2-bath suite on the first floor! Renovated throughout, the space offers a bright living room, full kitchen, and peaceful bedrooms. Relax on the wrap-around porch or stroll to Mount Holyoke College (less than 500 meters) and Village Commons for a peaceful afternoon. Perfect for family getaways or visiting nearby colleges with Amherst and Northampton just a short 20 minute drive away.

Amherst, Quiet, Private, Cozy Studio Apartment
This cozy studio is ideally located for exploring nearby colleges: UMass, Hampshire, Amherst, Mount Holyoke, and Smith. Nestled in the scenic Pioneer Valley, enjoy stunning landscapes, forests, and rivers, as well as cultural highlights like the Eric Carle Museum, Yiddish Book Center, and Emily Dickinson Museum. Just minutes from hiking trails, art galleries, gourmet dining, and music venues, our studio offers the perfect base for your Pioneer Valley adventure.
Popular amenities for Hampshire County family-friendly rentals
Family-friendly home rentals with a hot tub

The View Guest Suite - Amherst

Sweet suite, walk to town tout suite!

Serene South Deerfield Retreat

Hadley Hay House | No Cleaning fees!

Hilltown Cabin Hideaway: A River Runs Through It!

In style row house with private hot tub/pool table

Riverfront Getaway

Clean and sunny house near Smith College
Family- and pet-friendly home rentals

Tiny House Farm Retreat: Mountain Views, Fire pit

Bright Noho studio suite perfect walk to downtown

Berkshires Cottage by Lake. Year Round Adventures.

Cedar Wet Room w Soaking Tub

Stone n' Sky Lodge

Zachariah House Main St. Ashfield

Swiss Chalet Style Timberframe Home in Berkshires

House Above the Hollow
Family-friendly home rentals with a pool

Light-bathed comfort, wood + charm, right downtown

Sunset Ridge

Happy Valley getaway

Nestled Inn

Sweet cape near U Mass

NE Historical Mansion-pets and pet lovers welcome

High Field Farm

Enjoy every season the Berkshires have to offer.
Destinations to explore
- Rentals with a fireplace Hampshire County
- Pet-friendly rentals Hampshire County
- Rentals with outdoor seating Hampshire County
- Guest house rentals Hampshire County
- Rentals with pools Hampshire County
- Private suite rentals Hampshire County
- Flat rentals Hampshire County
- Bed and breakfasts Hampshire County
- Rentals with breakfast Hampshire County
- Rentals with a patio Hampshire County
- Rentals with a hot tub Hampshire County
- Smoking-friendly rentals Hampshire County
- House rentals Hampshire County
- Rentals with an EV charger Hampshire County
- Rentals with a kayak Hampshire County
- Rentals with a firepit Hampshire County
- Rentals with a washing machine and dryer Hampshire County
- Rentals with lake access Hampshire County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Taconic State Park
- Ski Sundown
- Norman Rockwell Museum
- Naumkeag
- Berkshire Botanical Garden
- Dcu Center
- Hancock Shaker Village
- University of Connecticut
- Mount Greylock
- Mount Holyoke College
- Smith College
- Clark University
- Connecticut Science Center
- University of Massachusetts Amherst
- Crooked Lake




